• Introduction
• Cabbage Key
• Captiva Island
• Sanibel Island
• North Captiva Island
• Island Hopping in Your Own Boat
• Getting There
• When to Go

Island Hopping in Your Own Boat

There is perhaps no better feeling than that of cruising the waters of Pine Island Sound from atop the bridge of your own boat and floating home. For those who agree and have moderate or greater experience piloting boats larger than 25 feet, a smart splurge is to rent one from Southwest Florida Yachts in North Fort Myers. The company offers a selection of beautifully maintained luxury trawlers and sailboats available for charter. Take a Grand Banks 42 ($4,500 for the week, plus $200 a day if you’d like a licensed captain onboard to teach you the ropes; swfyachts.com) down the Caloosahatchee River toward the Gulf of Mexico and turn north along the east coast of Sanibel. Spend an evening in the shallow waters of Tarpon Bay, then head north again along the Intracoastal Waterway for lunch at the clubhouse on Useppa, an elegant private island that provides charter captains courtesy docking. Pass another evening at the ’Tween Waters Marina on Captiva or off Gasparilla Island on the far side of Charlotte Harbor. Head home slowly, with the wind in your face, and make sure to stop whenever you wish to swim, fish, or just drift on the tide.

Less elegant perhaps but roomier and delivering a great value are the Gibson houseboats available for charter through Holiday Cruise Yacht Charters in Fort Myers ($2,400 for the week; holidaycruisehouseboats.com).

See Sanibel and Captiva Islands Travel Guide